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Issue 24, 1995
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Ionic ‘Diels–Alder’ reactions of hexa-3,5-dienyl trimethylsilyl ether and enones: X-ray structural determination of adduct stereostructure, and a stereoselective approach to trans-fused octalin systems

Abstract

The trimethylsilyl (TMS) and tert-butyldimethylsilyl (TBDMS) ethers of hexa-3,5-dien-1-ol react with cyclohexenones and an acyclic enone, methyl vinyl ketone (MVK), in the presence of 5–10 mol% of Me3SiOSO2CF3(TMSOTf) in MeCN to provide trans-fused adducts arising via ionic (Gassman-type) Diels–Alder reactions; structural confirmation for adduct stereochemistry for this type of reaction is provided by an X-ray structural determination.

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Article type: Paper
DOI: 10.1039/C39950002479
Citation: J. Chem. Soc., Chem. Commun., 1995,0, 2479-2480
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    Ionic ‘Diels–Alder’ reactions of hexa-3,5-dienyl trimethylsilyl ether and enones: X-ray structural determination of adduct stereostructure, and a stereoselective approach to trans-fused octalin systems

    R. K. Haynes, K. Lam, I. D. Williams and L. Yeung, J. Chem. Soc., Chem. Commun., 1995, 0, 2479
    DOI: 10.1039/C39950002479

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